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Lilly Dillon (Huston) is a veteran con artist who begins to rethink her life when her son Roy (Cusack), a small-time grifter, suffers a near-fatal injury when hit with a thrust from the blunt end of a baseball bat, right after a failed scam.

Lilly works for a bookmaker, Bobo Justus, handling playback at horse racing tracks – that is, she makes large cash bets to lower the odds of longshots. On her way to La Jolla for the horse races, she stops in Los Angeles to visit Roy, whom she has not seen in eight years. She finds him in pain and bleeding internally. When medical assistance finally comes, Lilly confronts the doctor, threatening to have him killed if her son dies.

At the hospital, Lilly meets and takes an instant dislike to Roy's girlfriend, Myra Langtry (Bening), who is a few years older than her son. Lilly urges her son to quit the grift, saying he literally does not have the stomach for it. Because she leaves late for La Jolla, she misses a race where the winner was paying 70–1. For this mistake, Bobo burns her hand with a cigar.

Myra, like Roy and Lilly, plays all the angles. When her landlord demands payment of late rent, she uses her sex appeal to lure him into bed and forget the rent. She makes a similar offer to a jeweler to get what she wants for a gem she is trying to pawn.

Upon leaving the hospital, Roy takes Myra to La Jolla for the weekend. On the train, she notices him conning a group of sailors in a rigged dice game. Myra reveals to Roy that she is also a grifter and is looking for a new partner for a long-con operation.

Myra describes her long association with another man, Cole, and how they took advantage of wealthy marks in business cons, including a greedy oil investor, Gloucester Hebbing. A flashback scene in a plush office building culminates in a fake FBI raid with a fake shooting of Myra to discourage Hebbing from going to the police.

Roy – who insists on working only short-term cons – resists the proposition, fearing she may try to dupe him herself. Myra, seeing Lilly's power over Roy, accuses him of having an incestuous interest in Lilly. Infuriated, Roy strikes her. Myra then plans her revenge. She lets it be known that Lilly has been stealing from Bobo over the years and stashing money in the trunk of her car. Lilly is warned by a friend and flees. Myra follows with the intention of killing her.

Roy is called by an FBI agent to identify his mother's body, found in a motel room with the face disfigured. While identifying it as Lilly's, he silently notes that there is no cigar burn on the corpse's hand. Coming back home, he finds Lilly trying to steal all of his money. Lilly, it is revealed, shot Myra in self-defense at the motel and arranged the scene to appear as though Myra's body was actually Lilly's.

Roy refuses to let Lilly depart with his money. A desperate Lilly is willing to try anything, first pleading with him, then attempting to seduce him, even going so far as to tempt Roy by claiming he is not really her son. Roy rejects her, disgusted. In anger, Lilly swings a suitcase at him and unintentionally breaks a drinking glass onto his neck, slashing an artery.

Lilly sobs convulsively while she packs up the money as her son bleeds to death on the floor. In the penultimate shot, she is seen dressed in red, riding an elevator that is heading down (Scorsese said in an interview that this scene symbolizes Lilly's descent into Hell). Then she gets into Roy's car and drives off into the night.

The project originated with Martin Scorsese who subsequently brought in Stephen Frears to direct while he produced.[1] Frears had just finished making Dangerous Liaisons and was looking for another project when Scorsese approached him.[2] The British filmmaker was drawn to Thompson's "tough and very stylistic" writing and described it, "as if pulp fiction meets Greek tragedy".[2] Scorsese looked for a screenwriter, and filmmaker Volker Schlöndorff recommended Donald Westlake.

Frears contacted Westlake who agreed to re-read the Thompson novel but, after doing so, turned the project down, citing the story as "too gloomy." Frears then phoned Westlake and convinced him that he saw the story as a positive one, if considered as a story of Lilly's drive to survive. Westlake changed his mind and agreed to write the adaptation.[1] Frears was unsuccessful, however, at convincing Westlake to write the script under his pseudonym "Richard Stark," a name he had used to write 20 noir-influenced crime novels from 1962 through 1974. (Stark's name appears in the film, though, on a sign reading "Stark, Coe and Fellows"; Westlake explains in the film's commentary track that he has written novels as Richard Stark, Tucker Coe and "some other fellows.")

Meanwhile, John Cusack had read Jim Thompson's novel in 1985 and was so impressed by it that he wanted to turn the book into a film himself.[3] When Cusack found out that Scorsese and Frears were planning an adaptation, he actively pursued a role in the project. Cusack has said that he saw the character of Roy Dillon as "a wonderfully twisted role to dive into."[3] To research his role, he studied with real grifters and learned card and dice tricks as well as sleight-of-hand tricks like the $20 switch that his character does in the film. He even successfully pulled off this trick at a bar on a bartender he knew well.[4]

For the role of Lilly, Frears originally considered Cher but she became too expensive after the success of Moonstruck.[5]Sissy Spacek also read the part of Lily Dillon.

Frears first contacted Anjelica Huston about playing Lilly in 1989 while she was filming Crimes and Misdemeanors but, after reading the script, she was unsure.[6] A few months later, Frears contacted Huston again to see if she was still interested.[6] He was reluctant to cast her because she looked like "a lady" and decided to cheapen her look with a bleached blond wig and "vulgar clothes."[2] Huston read the script again and felt more passionate about the part and was cast in the role. To research her part, she studied women dealers at card parlors in L.A. county.[6]

The shoot was emotionally challenging for Huston. After completing the final scene between Lilly and Roy, she was so drained from the experience that she ran from the set and the studio. It took her hours to recover.[6] After shooting the scene where Bobo Justus tortures Lilly for information, Huston was so affected by the rough quality of the scene (which did not make the final cut of the film) that she spent that night throwing up.[6]